WO2019221408A1 - Composition de résine de polycarbonate et produit moulé optique la comprenant - Google Patents

Composition de résine de polycarbonate et produit moulé optique la comprenant Download PDF

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Publication number
WO2019221408A1
WO2019221408A1 PCT/KR2019/004713 KR2019004713W WO2019221408A1 WO 2019221408 A1 WO2019221408 A1 WO 2019221408A1 KR 2019004713 W KR2019004713 W KR 2019004713W WO 2019221408 A1 WO2019221408 A1 WO 2019221408A1
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WO
WIPO (PCT)
Prior art keywords
polycarbonate resin
resin composition
weight
formula
optical molded
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2019/004713
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English (en)
Korean (ko)
Inventor
전병규
손영욱
황대현
홍무호
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to EP19802975.3A priority Critical patent/EP3702409B1/fr
Priority to JP2020518505A priority patent/JP6991322B2/ja
Priority to US16/756,090 priority patent/US11591475B2/en
Priority to CN201980004850.XA priority patent/CN111183182B/zh
Publication of WO2019221408A1 publication Critical patent/WO2019221408A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
    • C09B1/5035—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone only amino and hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses

Definitions

  • the present invention relates to a polycarbonate resin composition having excellent thermal stability and optical properties, and to an optical molded article including the same.
  • Polycarbonate is applied to various fields such as exterior materials, automotive parts, building materials, and optical parts of electric and electronic products due to its excellent impact strength, numerical stability, heat resistance, and transparency.
  • the present invention is to provide a polycarbonate resin composition having excellent heat resistance and excellent optical properties by introducing a dye of a combination of two kinds of specific additives.
  • this invention is providing the optical molded article manufactured from the said polycarbonate resin composition.
  • an optical molded article comprising the polycarbonate resin composition.
  • a copolycarbonate according to a specific embodiment of the present invention, a manufacturing method thereof, and a molded article including the same will be described in more detail.
  • the terminology is for the purpose of referring only to particular embodiments and is not intended to limit the invention unless expressly stated otherwise. 2019/221408 1 »(: 1 ⁇ 1 ⁇ 2019/004713
  • first component may also be referred to as the second component, and similarly, the second component may be referred to as the first component.
  • the first component may also be referred to as the second component, and similarly, the second component may be referred to as the first component.
  • the transparency of polycarbonate according to the applied product range, for example, the transmittance in a specific wavelength range depending on the purpose of use when applied to an optical product (eg lens), etc. It was necessary to lower.
  • the additive is used simply for the purpose of increasing the shielding rate, the heat resistance is significantly lowered under high temperature conditions, and there is a problem that polymer deformation or discoloration occurs during the manufacturing process.
  • the present inventors have realized a low transmittance in a specific wavelength range and a low yellowing index change in a high temperature condition by using a combination of a specific additive and two dyes having excellent absorption at a predetermined wavelength, and thus have excellent heat resistance and a specific wavelength.
  • a polycarbonate resin composition having a high shielding rate in the region was developed.
  • the degree of modification or color change of the polymer is remarkably small even under high temperature trimming conditions during the manufacturing process.
  • the product is actually used can exhibit excellent physical properties without deformation even in a high temperature environment.
  • when used as a lens it can exhibit a good shielding ratio in a specific visible light region (410ä), it can be applied to a wide range of general, industrial, sports, special applications, etc. 2019/221408 1 »(: 1 ⁇ 1 ⁇ 2019/004713
  • Polycarbonate resin composition according to an embodiment of the present invention satisfies a transmittance of 7% or less at 410 ? By satisfying the transmittance in the above range and the yellowing index change value to be thrown at the same time, all the above-described physical properties can be satisfied when applied to the product.
  • the transmittance at 410ä is greater than 7%, there is a problem that cannot be applied to various optical molded products such as general use, industrial use, sport use, and special use.
  • the transmittance at 4101 ⁇ is preferably 5% or less, and more preferably 4.5% or less, in which case the desired effect of the present invention may be increased.
  • the yellowing index change value represented by the following general formula (1) satisfies 0.5 or less, and simultaneously satisfies the yellowing index change value (s) and transmittance in the above range, In application, all of the above-described properties can be satisfied:
  • ⁇ ⁇ 1 (340 ° 0- ⁇ 1 (285 ° 0
  • the parameter of the yellowing index change value (s) in the above range means an index showing excellent heat resistance even in a high temperature buy process when manufacturing a product using a polycarbonate resin composition, and at a high temperature of 2851: to 340 ° Even if the temperature is changed, it shows a significantly low yellowing index change, which means that it exhibits excellent heat resistance even when the product is applied and placed under high temperature environmental conditions.
  • the yellowness index change value is more than 0.5, heat resistance is lowered and transmittance is lowered, so that it is not suitable for use as a lens.
  • the yellowing index change value is preferably less than 0.3, more preferably less than 0.1, in this case, the desired effect of the present invention could be increased. 2019/221408 1 »(: 1 ⁇ 1 ⁇ 2019/004713
  • Polycarbonate resin composition according to an embodiment of the present invention is a polycarbonate resin; Pentaerythritol tetrastearate
  • the term 1 polycarbonate used in the present invention means a polymer produced by reacting a diphenol compound, a phosgene, a carbonate ester, or a combination thereof.
  • Polycarbonate resins are very excellent in heat resistance, impact resistance, mechanical strength, transparency, and the like, and are widely used in the manufacture of compact discs, transparent sheets, packaging materials, automobile bumpers, UV blocking films, optical lenses, and the like.
  • diphenol type compound hydroquinone, resorcinol, 4, 4'- dihydroxy diphenyl, 2, 2-bis (4-hydroxyphenyl) propane (also called bisphenol-show), 2, 4-bis (4-hydroxyphenyl) -2-methylbutane, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) cyclonucleic acid, 2,2-bis (3-chloro -4-hydroxyphenyl) propane, 2, 2-bis (3, 5- dimethyl- 4-hydroxyphenyl) propane, 2, 2- bis (3, 5- dichloro- 4-hydroxyphenyl) propane, 2 , 2-bis (3,5-dibromo-4-hydroxyphenyl) propane, bis (4-hydroxyphenyl) sulfoxide, bis (4-hydroxyphenyl) ketone, bis (4-hydroxyphenyl) Ether and the like.
  • 4, 4'- dihydroxy diphenyl, 2, 2-bis (4-hydroxyphenyl) propane may be used, in this case the structure of the polycarbonate resin is
  • the polycarbonate resin may be a mixture of copolymers prepared from two or more diphenols.
  • the polycarbonate may be a linear polycarbonate,-branched (carbonated) polycarbonate, polyester carbonate copolymer resin and the like.
  • linear polycarbonates examples include polycarbonates prepared from bisphenols.
  • branched polycarbonates include those produced by reacting polyfunctional aromatic compounds such as trimellitic anhydride and trimellitic acid with diphenols and carbonates.
  • the polyfunctional aromatic compound may be included in an amount of 0.05 mol% to 2 mol% based on the total amount of the branched polycarbonate.
  • polyester carbonate copolymer resin what was manufactured by making bifunctional carboxylic acid react with diphenols and a carbonate is mentioned.
  • carbonate diaryl carbonates such as diphenyl carbonate, ethylene carbonate, and the like may be used.
  • the polycarbonate resin according to the present invention satisfies the melt flow rate (MFR, Melt flow rate) according to ASTM D1238 5 to 15g / 10min.
  • MFR Melt flow rate
  • ASTM D1238 melt flow rate
  • the melt flow rate was measured under load conditions of 1.2 kg at 300 ° C. according to ASTM D1238.
  • melt flow rate is less than 5 g / min, the workability is lowered, there may be a problem of productivity degradation, when the melt flow rate is greater than 15 g / min, the resin flow is exceeded under the processing conditions to cause surface defects in the molded product May occur.
  • the melt flow rate is preferably 6 to 13g / 10min, more preferably 7 to 10g / 10min, in this case, the desired effect of the present invention can be increased.
  • the polycarbonate resin has a weight average molecular weight of 10,000 g / mol to 50,000 g / mol, preferably 25,000 g / mol to 35,000 g / mol. It is excellent in moldability and workability in the said range.
  • Pantaerythritol tetrastearate, PETS Pantaerythritol tetrastearate
  • Pentaerythritol tetrastearate component according to the present invention is a component that serves to improve the thermal stability and at the same time to improve the shielding in a specific wavelength range, and is used in combination with the black and blue dyes described below to effect the effect It can be maximized.
  • the pentaerythritol tetrastearate may be included in an amount of 0.05 to 5 parts by weight, and preferably 0.1 to 1 part by weight, based on 100 parts by weight of polycarbonate resin.
  • the pentaerythritol tetrastearate may be included in an amount of 0.05 to 5 parts by weight, and preferably 0.1 to 1 part by weight, based on 100 parts by weight of polycarbonate resin.
  • it is possible to implement excellent heat resistance and shielding it is preferable to implement the shielding secondary effect in the heat and specific wavelength range.
  • it is contained less than 0.05 parts by weight it is difficult to implement the desired effect in a small amount, if it is included in 5 parts by weight, a problem may occur that the mechanical strength is lowered.
  • the present invention is a component for improving the shielding in a specific wavelength region by using a combination of a black dye and a blue dye, and can be used in combination with the? £ 15 component described above to realize the effect of improving the shielding and heat resistance.
  • the black dye is specifically 0.1. It may be a compound of Pigment Black 32 (Perylene Black). ⁇ 32 (3 ⁇ 411101) 13 urine 70) may be used.
  • the black dye can effectively block light in the full wavelength range, When used in combination with a blue dye it is desirable to implement a shielding suitable for application to the lens.
  • the black dye may be included in 1.0 * 10 one 4 to 1.0 * 10 _1 parts by weight based on 100 parts by weight of polycarbonate resin, preferably 1.0 * 10 4 to
  • 1.0 * 10 _2 parts by weight more preferably 1.1 * 10 3 to 2.0 * 10 ⁇ 3 parts by weight may be included.
  • the blue dye may be a compound of Formula 2 (CAS No. 81-48-1), and Blue G (Macrolex Violet B Gran) of Lanxess may be used as a commercially available product.
  • the blue dye may preferably be a Redish sh blue series.
  • the blue dye serves to improve the yellowing of the resin, and at the same time,
  • the blue dye is 1.0 * 10 one, based on 100 parts by weight of polycarbonate resin
  • 4 to l.CKKT may be included in an amount of 1 part by weight, preferably 1.0 * 10 4 to 1.0 * 10 2 parts by weight, more preferably 1.5 * l (r 3 to 2.5 * 10 ⁇ 3 parts by weight).
  • it is difficult to implement the desired effect in a small amount when included in an amount of 1.0 * 10 -1 parts by weight, there is a disadvantage in that it is commercially applicable due to a decrease in YI and a decrease in permeability. 2019/221408 1 »(1 ⁇ 1 ⁇ 2019/004713
  • the resin composition may be selected from the group consisting of antioxidants, heat stabilizers, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, optical brighteners, ultraviolet absorbers, and radiation absorbers commonly used in the art. It may further comprise an additive selected from the species.
  • Optical molded article may be selected from the group consisting of antioxidants, heat stabilizers, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, optical brighteners, ultraviolet absorbers, and radiation absorbers commonly used in the art. It may further comprise an additive selected from the species.
  • this invention provides the optical molded article containing the said resin composition.
  • the optical molded article is a lens, and is suitable for use in an illumination lens or spectacle lens.
  • the polycarbonate resin composition according to the present invention has excellent heat resistance and shielding properties, it can be usefully used as an optical molded article.
  • Method for producing a molded article may be prepared by a method commonly used in the art. For example, it is preferable to mix the above-mentioned polycarbonate resin, pentaerythritol tetrastearate, black dye, and blue dye with additives as necessary, melt kneading them into pellets, and to carry out injection molding in a desired form.
  • the melt kneading is performed by a method commonly used in the art, for example, a ribbon blender, a Henschel mixer, a Banbury mixer, a drum tumbler, a single screw extruder, a two-screw screw injector, a corneader, a dead screw injector, or the like. It can be carried out.
  • mixing can be suitably adjusted as needed.
  • Molding methods such as the bending molding method, the compression molding method, the calender molding method, and the rotation molding method can be applied.
  • the resin composition according to the present invention has excellent heat resistance, and thus, there is little polymer modification or yellowing in the melt kneading process or the injection process described above. Do.
  • the size, thickness, etc. of the molded article may be appropriately adjusted according to the purpose of use, and the shape of the light guide plate may also have the form of a flat plate or a curved surface according to the purpose of use.
  • the optical molded article manufactured from the polycarbonate resin composition which can exhibit the outstanding optical characteristic also in high temperature conditions can be provided.
  • a polycarbonate resin composition was prepared by mixing the respective additive components in the amounts shown in Table 1 based on 100 parts by weight of the polycarbonate resin composition.
  • the yellowness index was measured at 1050 nm.
  • the yellowing index was measured at 285 ° C and 34CTC while heating at 285 ° C for 340 ° C for 20 minutes, and the yellowing index change value was calculated according to the following general formula 1 and the results are shown in Table 2 below.
  • AYI YI (340 ° C)-YI (285 ° C)
  • the heat resistance under the high temperature condition is significantly lowered, and the variation in sulfur and variability is significantly increased, or the transmittance is increased at 410ä, which is not suitable for use in optical molded products, especially lenses. It was confirmed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne : une composition de résine de polycarbonate utilisant, en combinaison, un additif spécifique et deux types de colorants, présentant ainsi une stabilité thermique et des propriétés optiques excellentes; et un produit moulé optique la comprenant.
PCT/KR2019/004713 2018-05-15 2019-04-18 Composition de résine de polycarbonate et produit moulé optique la comprenant Ceased WO2019221408A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP19802975.3A EP3702409B1 (fr) 2018-05-15 2019-04-18 Composition de résine de polycarbonate et produit optique moulé la comprenant
JP2020518505A JP6991322B2 (ja) 2018-05-15 2019-04-18 ポリカーボネート樹脂組成物およびこれを含む光学成形品
US16/756,090 US11591475B2 (en) 2018-05-15 2019-04-18 Polycarbonate resin composition and optical molded product including the same
CN201980004850.XA CN111183182B (zh) 2018-05-15 2019-04-18 聚碳酸酯树脂组合物和包含其的光学模制品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0055589 2018-05-15
KR1020180055589A KR102209392B1 (ko) 2018-05-15 2018-05-15 폴리카보네이트 수지 조성물 및 이를 포함하는 광학 성형품

Publications (1)

Publication Number Publication Date
WO2019221408A1 true WO2019221408A1 (fr) 2019-11-21

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PCT/KR2019/004713 Ceased WO2019221408A1 (fr) 2018-05-15 2019-04-18 Composition de résine de polycarbonate et produit moulé optique la comprenant

Country Status (7)

Country Link
US (1) US11591475B2 (fr)
EP (1) EP3702409B1 (fr)
JP (1) JP6991322B2 (fr)
KR (1) KR102209392B1 (fr)
CN (1) CN111183182B (fr)
TW (1) TWI695862B (fr)
WO (1) WO2019221408A1 (fr)

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CN119350831A (zh) * 2024-11-18 2025-01-24 上海金发科技发展有限公司 一种高饱和度荧光橙聚酯类组合物及其制备方法和应用

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JP2020535299A (ja) 2020-12-03
KR20190130889A (ko) 2019-11-25
EP3702409A1 (fr) 2020-09-02
TW202003686A (zh) 2020-01-16
US11591475B2 (en) 2023-02-28
CN111183182A (zh) 2020-05-19
EP3702409A4 (fr) 2021-03-10
KR102209392B1 (ko) 2021-01-28
CN111183182B (zh) 2022-06-14
TWI695862B (zh) 2020-06-11
EP3702409B1 (fr) 2023-07-19

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